# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       TMCCABE@tcd.ie
_publ_contact_author_name        'Tom McCabe'
_publ_author_name                S.Connon

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 859316'
#TrackingRef 'SHELXLcap500.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 N O2 S'
_chemical_formula_weight         329.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.4220(17)
_cell_length_b                   10.230(2)
_cell_length_c                   20.787(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1790.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5794
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   Crystalclear

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn 724'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8407
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_sigmaI/netI    0.0678
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3084
_reflns_number_gt                2746
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Crystalclear
_computing_cell_refinement       Crystalclear
_computing_data_reduction        Crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Shelxtl
_computing_publication_material  'Shelxtl and Mercury'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1800P)^2^+0.2325P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration ad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.22(19)
_refine_ls_number_reflns         3084
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0639
_refine_ls_wR_factor_ref         0.2624
_refine_ls_wR_factor_gt          0.1936
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.36333(15) 0.33096(12) 0.20691(6) 0.0381(4) Uani 1 1 d . . .
N1 N 0.1999(6) -0.0374(4) 0.1684(2) 0.0392(10) Uani 1 1 d . . .
C19 C 0.2647(6) 0.0756(5) 0.2062(3) 0.0386(11) Uani 1 1 d . . .
H19A H 0.3600 0.0489 0.2289 0.046 Uiso 1 1 calc R . .
H19B H 0.1871 0.1041 0.2376 0.046 Uiso 1 1 calc R . .
C18 C 0.3035(6) 0.1881(4) 0.1599(2) 0.0333(10) Uani 1 1 d . . .
H18 H 0.2090 0.2096 0.1345 0.040 Uiso 1 1 calc R . .
C17 C 0.1751(6) 0.3798(5) 0.2428(2) 0.0385(11) Uani 1 1 d . . .
H17A H 0.1276 0.3038 0.2631 0.046 Uiso 1 1 calc R . .
H17B H 0.1964 0.4433 0.2764 0.046 Uiso 1 1 calc R . .
C2 C -0.3037(7) 0.6218(5) 0.0738(2) 0.0379(11) Uani 1 1 d . . .
C6 C -0.0328(6) 0.6183(5) 0.1322(2) 0.0350(11) Uani 1 1 d . . .
H6 H -0.0145 0.7015 0.1157 0.042 Uiso 1 1 calc R . .
C11 C 0.4379(6) 0.1551(4) 0.1157(2) 0.0322(10) Uani 1 1 d . . .
C7 C 0.0796(6) 0.5629(5) 0.1707(2) 0.0358(11) Uani 1 1 d . . .
H7 H 0.1724 0.6084 0.1799 0.043 Uiso 1 1 calc R . .
C8 C 0.0562(6) 0.4378(4) 0.1966(2) 0.0316(10) Uani 1 1 d . . .
C12 C 0.4167(7) 0.1612(5) 0.0486(3) 0.0425(12) Uani 1 1 d . . .
H12 H 0.3195 0.1876 0.0319 0.051 Uiso 1 1 calc R . .
O2 O 0.0791(5) -0.0213(5) 0.1380(2) 0.0594(12) Uani 1 1 d . . .
O1 O 0.2718(6) -0.1423(4) 0.1707(2) 0.0615(12) Uani 1 1 d . . .
C9 C -0.0832(7) 0.3719(5) 0.1800(2) 0.0373(11) Uani 1 1 d . . .
H9 H -0.0998 0.2876 0.1954 0.045 Uiso 1 1 calc R . .
C16 C 0.5870(6) 0.1174(5) 0.1391(3) 0.0432(12) Uani 1 1 d . . .
H16 H 0.6034 0.1125 0.1833 0.052 Uiso 1 1 calc R . .
C10 C -0.1971(6) 0.4294(5) 0.1411(2) 0.0355(11) Uani 1 1 d . . .
H10 H -0.2894 0.3835 0.1314 0.043 Uiso 1 1 calc R . .
C5 C -0.1763(6) 0.5538(5) 0.1164(2) 0.0362(11) Uani 1 1 d . . .
C15 C 0.7102(7) 0.0873(6) 0.0978(3) 0.0535(15) Uani 1 1 d . . .
H15 H 0.8093 0.0644 0.1140 0.064 Uiso 1 1 calc R . .
C14 C 0.6846(8) 0.0916(6) 0.0321(3) 0.0550(16) Uani 1 1 d . . .
H14 H 0.7663 0.0694 0.0041 0.066 Uiso 1 1 calc R . .
C4 C -0.4285(8) 0.5267(7) 0.0496(3) 0.0598(17) Uani 1 1 d . . .
H4A H -0.5060 0.5731 0.0246 0.090 Uiso 1 1 calc R . .
H4B H -0.4797 0.4856 0.0856 0.090 Uiso 1 1 calc R . .
H4C H -0.3788 0.4612 0.0234 0.090 Uiso 1 1 calc R . .
C1 C -0.3836(10) 0.7286(8) 0.1156(4) 0.077(2) Uani 1 1 d . . .
H1A H -0.4572 0.7774 0.0898 0.115 Uiso 1 1 calc R . .
H1B H -0.3039 0.7864 0.1323 0.115 Uiso 1 1 calc R . .
H1C H -0.4394 0.6881 0.1506 0.115 Uiso 1 1 calc R . .
C3 C -0.2241(9) 0.6834(8) 0.0152(3) 0.0661(19) Uani 1 1 d . . .
H3A H -0.1817 0.6158 -0.0119 0.099 Uiso 1 1 calc R . .
H3B H -0.1396 0.7397 0.0290 0.099 Uiso 1 1 calc R . .
H3C H -0.3008 0.7334 -0.0085 0.099 Uiso 1 1 calc R . .
C13 C 0.5382(9) 0.1287(6) 0.0076(3) 0.0563(16) Uani 1 1 d . . .
H13 H 0.5223 0.1315 -0.0366 0.068 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0302(6) 0.0303(6) 0.0537(7) -0.0037(5) 0.0002(5) -0.0026(5)
N1 0.037(2) 0.033(2) 0.047(2) 0.0008(19) 0.011(2) -0.003(2)
C19 0.040(3) 0.034(2) 0.042(2) 0.001(2) 0.012(2) -0.007(2)
C18 0.030(2) 0.025(2) 0.045(2) 0.002(2) -0.002(2) -0.002(2)
C17 0.040(3) 0.035(2) 0.041(2) -0.007(2) 0.004(2) 0.005(2)
C2 0.037(3) 0.034(2) 0.042(2) 0.002(2) -0.005(2) -0.006(2)
C6 0.037(3) 0.021(2) 0.047(2) 0.0049(19) 0.001(2) -0.008(2)
C11 0.030(2) 0.0194(19) 0.047(3) 0.0016(19) 0.000(2) 0.0000(19)
C7 0.031(3) 0.030(2) 0.046(3) -0.001(2) 0.006(2) -0.006(2)
C8 0.037(3) 0.026(2) 0.031(2) -0.0052(18) 0.0059(18) -0.0022(19)
C12 0.044(3) 0.039(3) 0.045(3) -0.002(2) 0.000(2) -0.005(2)
O2 0.044(2) 0.058(3) 0.076(3) -0.009(2) -0.011(2) -0.011(2)
O1 0.071(3) 0.034(2) 0.079(3) -0.008(2) 0.009(3) 0.008(2)
C9 0.041(3) 0.025(2) 0.046(2) 0.002(2) 0.002(2) -0.003(2)
C16 0.033(3) 0.038(3) 0.058(3) 0.009(2) 0.003(2) 0.006(2)
C10 0.035(3) 0.030(2) 0.041(2) -0.0030(19) -0.001(2) -0.005(2)
C5 0.034(3) 0.031(2) 0.044(2) 0.002(2) 0.000(2) -0.002(2)
C15 0.034(3) 0.041(3) 0.086(4) 0.008(3) 0.006(3) 0.004(2)
C14 0.050(3) 0.041(3) 0.075(4) -0.005(3) 0.029(3) -0.003(3)
C4 0.058(4) 0.049(3) 0.072(4) 0.011(3) -0.024(3) -0.009(3)
C1 0.076(5) 0.073(5) 0.082(5) -0.019(4) -0.032(4) 0.032(4)
C3 0.063(4) 0.064(4) 0.071(4) 0.029(3) -0.011(3) -0.007(4)
C13 0.060(4) 0.054(4) 0.054(3) -0.015(3) 0.010(3) -0.009(3)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C17 1.822(5) . ?
S1 C18 1.829(5) . ?
N1 O2 1.209(6) . ?
N1 O1 1.234(6) . ?
N1 C19 1.499(7) . ?
C19 C18 1.535(7) . ?
C18 C11 1.497(7) . ?
C17 C8 1.510(7) . ?
C2 C4 1.518(8) . ?
C2 C3 1.528(8) . ?
C2 C1 1.550(9) . ?
C2 C5 1.556(7) . ?
C6 C7 1.363(7) . ?
C6 C5 1.416(7) . ?
C11 C16 1.401(7) . ?
C11 C12 1.407(7) . ?
C7 C8 1.402(7) . ?
C8 C9 1.397(7) . ?
C12 C13 1.372(8) . ?
C9 C10 1.386(7) . ?
C16 C15 1.381(8) . ?
C10 C5 1.383(7) . ?
C15 C14 1.384(10) . ?
C14 C13 1.386(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 S1 C18 101.4(2) . . ?
O2 N1 O1 123.5(5) . . ?
O2 N1 C19 118.4(5) . . ?
O1 N1 C19 118.1(5) . . ?
N1 C19 C18 109.1(4) . . ?
C11 C18 C19 112.1(4) . . ?
C11 C18 S1 107.5(3) . . ?
C19 C18 S1 108.9(3) . . ?
C8 C17 S1 115.1(3) . . ?
C4 C2 C3 107.7(5) . . ?
C4 C2 C1 109.7(6) . . ?
C3 C2 C1 110.3(6) . . ?
C4 C2 C5 112.3(4) . . ?
C3 C2 C5 109.6(5) . . ?
C1 C2 C5 107.2(4) . . ?
C7 C6 C5 122.3(4) . . ?
C16 C11 C12 118.0(5) . . ?
C16 C11 C18 121.9(5) . . ?
C12 C11 C18 120.2(4) . . ?
C6 C7 C8 120.5(5) . . ?
C9 C8 C7 117.6(5) . . ?
C9 C8 C17 121.7(4) . . ?
C7 C8 C17 120.6(5) . . ?
C13 C12 C11 120.7(5) . . ?
C10 C9 C8 121.4(5) . . ?
C15 C16 C11 121.3(5) . . ?
C5 C10 C9 121.3(5) . . ?
C10 C5 C6 116.8(5) . . ?
C10 C5 C2 122.4(5) . . ?
C6 C5 C2 120.8(4) . . ?
C16 C15 C14 119.3(6) . . ?
C15 C14 C13 120.6(5) . . ?
C12 C13 C14 120.1(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N1 C19 C18 -60.7(6) . . . . ?
O1 N1 C19 C18 120.1(5) . . . . ?
N1 C19 C18 C11 -66.9(6) . . . . ?
N1 C19 C18 S1 174.3(3) . . . . ?
C17 S1 C18 C11 167.3(3) . . . . ?
C17 S1 C18 C19 -71.1(4) . . . . ?
C18 S1 C17 C8 -70.7(4) . . . . ?
C19 C18 C11 C16 -56.8(6) . . . . ?
S1 C18 C11 C16 62.8(5) . . . . ?
C19 C18 C11 C12 123.2(5) . . . . ?
S1 C18 C11 C12 -117.3(4) . . . . ?
C5 C6 C7 C8 -0.1(7) . . . . ?
C6 C7 C8 C9 1.7(7) . . . . ?
C6 C7 C8 C17 -175.8(4) . . . . ?
S1 C17 C8 C9 110.9(5) . . . . ?
S1 C17 C8 C7 -71.7(5) . . . . ?
C16 C11 C12 C13 1.2(8) . . . . ?
C18 C11 C12 C13 -178.7(5) . . . . ?
C7 C8 C9 C10 -2.1(7) . . . . ?
C17 C8 C9 C10 175.4(4) . . . . ?
C12 C11 C16 C15 0.1(8) . . . . ?
C18 C11 C16 C15 -179.9(5) . . . . ?
C8 C9 C10 C5 0.9(8) . . . . ?
C9 C10 C5 C6 0.7(7) . . . . ?
C9 C10 C5 C2 -178.7(4) . . . . ?
C7 C6 C5 C10 -1.1(7) . . . . ?
C7 C6 C5 C2 178.3(4) . . . . ?
C4 C2 C5 C10 -14.2(7) . . . . ?
C3 C2 C5 C10 -133.9(6) . . . . ?
C1 C2 C5 C10 106.3(6) . . . . ?
C4 C2 C5 C6 166.4(5) . . . . ?
C3 C2 C5 C6 46.7(7) . . . . ?
C1 C2 C5 C6 -73.0(7) . . . . ?
C11 C16 C15 C14 -1.5(9) . . . . ?
C16 C15 C14 C13 1.5(9) . . . . ?
C11 C12 C13 C14 -1.2(9) . . . . ?
C15 C14 C13 C12 -0.2(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.654
_refine_diff_density_rms         0.155